Salicylic acid salt of 8-(5&#39;-isopropylaminoamylamino)-6-methoxyquinoline



Patented Apr. 29, 1952 UNITED STATES PATENT OFFICE SALICYLIC ACID SALT F8- ('-ISOPR.OPYL- AMINOAMYLAMINO) 6 -METHOXYQUINO- LINE Charles F.Geschickter, Rock Creek Hills, and Martin I. Rubin, Silver Spring, Md.,assignors to GeschickterFund for Medical Research, Inc., New York, N.Y., a corporation of New York No Drawing. Application September 30,1949, Serial No. 118,997

1 Claim.

Where efiective, they afford symptomatic rather than permanent relief orcure. The same is true of desensitizing injections of protein substanceswhich have the added disadvantage of requiring elaborate intradermaltesting to determine the nature of the sensitizing agent or allergen.

In accordance with the present invention certain new antihistaminesubstances have been found which concentrate especially in therespiratory epithelium andwhich had a prolonged duration so that a serumlevel could be established and maintained. The particular antihistamineswhich are the subject of the persent invention are amino-quinolines andin particular the monoknown compound 8-(5'-isopropylaminoamylamino)-6-methoxy-quinoline for 'a short period of time with a solution of aquantity in slight molar excess of salicyclic acid in ethanol. Thereaction product was then concentrated to dryness and extracted with 3portions of hot boiling (70-90 C.) petroleum ether. The hot petroleumether solution was decanted and the residue dried. The residue was thensuitably formed into 15 mg.

capsules.

Example I 4 gs. of 8-(5-isopropylaminoamylamino)-6- methoxyquinolinewere boiled for 15 minutes salicylates of 6 methoxy 8 substitutedquinolines.

The particular salicylates involved are the monosalicylates of compoundsrepresented byv the following formula:

wherein R is a poly methylene chain of from 2 to 6 carbon atoms and R1is an alkyl radical of from 2 to 6 carbon atoms. An especially desirablecompound was the mono-salicylate of 8-(5'- isopropylaminoamylamino) -6-methoxyquinoline. This compound was administered to a number of patientsand it was found that plasma levels as high as .1 mg. per liter could beobtained on'daily doses as low as 60 mg. In addition the compound showed90% retention on a daily dose in the tissue and body fluids with a highconcentration in the respiratory tissue. It was found to have excellentresults in various types of allergy and common cold and in cases ofchronic sinusitis. Undesirable side efiects were not noticeable insubstantially all cases.

The salicylate salt was prepared by boiling the with a solution of 5 gs.of salicyclic acid in 20 cc. of ethanol, concentrated to dryness andextracted with 3 portions of hot (-90 C.) boiling petroleum ether. Thehot petroleum ether solution was decanted and the residue showed thecorrect elementary values for the salicylate salt.

It will be obvious to those skilled in the art that various changes maybe made without departing from the spirit of the invention and thereforethe invention is not limited to What is described in the specificationbut only as indicated in the appended claim.

What is claimed is:

A new compound consisting of the salicyclic acid salt of8-(5-isopropylaminoamylamino)-6- methoxyquinoline.

CHARLES F. GESCHICKTER. MARTIN I. RUBIN.

REFERENCES CITED The following references are of record in the file ofthis patent:

Wiselogle: Survey of Antimalarial Drugs, 1941-1945" (J. W. Edwards; AnnArbor, Mich., 1946), vol. I, pages 109-124; vol. II, part 2, page 1183.

Fischel: Proc. Soc. Exptl. Biol. Med., vol. 66, pp. 537-541 (1947).

Huttrer: Enzymologia, vol. XII, page 321 (1948).

Beiler: J. Am. Pharm. Assoc. (Sci. Ed.), vol. 37, pp. 315-317 (June1949).

